63492-69-3

Basic information

• Product Name: griffonin
• Synonyms: griffonin;(2Z)-[4β,5α-Dihydroxy-6β-(β-D-glucopyranosyloxy)-2-cyclohexene-1-ylidene]acetonitrile;[(1Z,4R)-6β-(β-D-Glucopyranosyloxy)-4β,5α-dihydroxy-2-cyclohexen-1-ylidene]acetonitrile;NSC 290807;(2Z)-2-[(4R,5S,6S)-6-(beta-D-Glucopyranosyloxy)-4,5-dihydroxy-2-cyclohexen-1-ylidene]acetonitrile;lithosprMoside;Acetonitrile,2-[(4R,5S,6S)-6-(b-D-glucopyranosyloxy)-4,5-dihydroxy-2-cyclohexen-1-ylidene]-,(2Z)-;Lithospermoside Griffonin
• CAS NO: 63492-69-3
• Molecular Formula: C₁₄H₁₉NO₈
• Molecular Weight: 329.3026
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 63492-69-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 271℃ (DEC.)
• Boiling Point: 662.4 °C at 760 mmHg
• Flash Point: 354.4 °C
• Appearance: /
• Density: 1.61
• Vapor Pressure: 2.3E-20mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 12.71±0.60(Predicted)
• CAS DataBase Reference: griffonin(CAS DataBase Reference)
• NIST Chemistry Reference: griffonin(63492-69-3)
• EPA Substance Registry System: griffonin(63492-69-3)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 63492-69-3(Hazardous Substances Data)

Usage

Description

Griffonin, derived from the roots of Semiquilegia adoxides, is a bioactive compound with significant anti-neutrophilic inflammatory properties. It has the potential to be utilized in various applications due to its ability to modulate immune responses and exhibit anti-inflammatory effects.

Uses

Used in Pharmaceutical Industry:
Griffonin is used as an anti-inflammatory agent for its ability to reduce neutrophilic inflammation. This property makes it a promising candidate for the development of treatments targeting inflammatory conditions and diseases.
Used in Research and Development:
Griffonin is also used as a research tool to study the underlying mechanisms of neutrophilic inflammation and its role in various diseases. This can lead to a better understanding of the inflammatory processes and the development of novel therapeutic strategies.

Upstream product

• 63568-00-3 (2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile 
• 561023-24-3 (2E)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile 

Relevant articles and documents

Total synthesis of (-)-lithospermoside

The total synthesis of the naturally occurring noncyanogenic cyanoglucoside (-)-lithospermoside (1) was achieved starting from optically pure oxatrinorbornenone (+)-2 in 12 steps and 10% overall yield. The key step of the synthesis, the glycosidation, turned out to be very sensitive to steric hindrance, and we had, therefore, to optimize the choice of the protection used for the two other OH functions of the aglycone. Finally, the desired β-D-glucoside 15 was obtained in a very good yield (72%) under Koenigs - Knorr-glycosidation conditions, closely related to those used for the total synthesis of (-)-bauhinin.